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Compare 239 Vacation Homes in Ashland with updated reviews, rates, and availability.

City Comfort: 3BDR Walkable Retreat

10.0 out of 10, Exceptional, (15)
"We were a family group in town to visit our sister several miles away. This home was lovely, well-equipped, super comfortable. The neighborhood was very quiet with dedicated parking. The upstairs bedrooms were a bit overheated at night and the floors / stairs creaked as mentioned by other reviewers, but nothing out of the norm for an older house. Will definitely try to stay here again!"
The price is SAR 701
SAR 1,909 total
includes taxes & fees
23 Mar - 24 Mar
City Comfort: 3BDR Walkable Retreat

Premier Downstairs Flat in Perfect Down Town Location

10.0 out of 10, Exceptional, (48)
"Great location - close to restaurants and shops! "
Premier Downstairs Flat in Perfect Down Town Location

California Cottage: Downtown!

9.8 out of 10, Exceptional, (22)
"We had a fun weekend even though it rained the whole time! We walked a short block and we're right in the downtown area. Great restaurants and fun shopping. The cottage was very comfortable and clean. "
The price is SAR 427
SAR 853 total
includes taxes & fees
24 Feb - 25 Feb
California Cottage: Downtown!

ZZ ZANY ZOO II - Townhome, with Carport & Garage

10.0 out of 10, Exceptional, (80)
"Adorable family-friendly theme with holiday spirit made for a memorable vacation."
ZZ ZANY ZOO II - Townhome, with Carport & Garage

232-Duplex-Private Bathroom-Mountain View

10.0 out of 10, Exceptional, (35)
"This has become our favorite place to stay in Ashland. We go there often to play at Mt. Ashland and to enjoy the Shakespeare Festival. This beautiful condo has everything we need with amazing views and a great coffee shop right across the street. We don't need to drive to enjoy downtown Ashland, everything is walking distance. It really has become a home away from home for us. "
232-Duplex-Private Bathroom-Mountain View

Pet-Friendly Medford Vacation Rental w/ Yard!

9.2 out of 10, Wonderful, (7)
"Great cozy location"
Pet-Friendly Medford Vacation Rental w/ Yard!

Jacksonville Mountain Retreat

9.6 out of 10, Exceptional, (61)
"This is a very nice home. "
Jacksonville Mountain Retreat

Three bedroom with king beds, 2 & a half bathroom. 2146 square foot house.

9.6 out of 10, Exceptional, (39)
"House was amazing, stayed with family and new grand baby. Everything you could need and the split level was perfect for us! Definitely will rent again next time were in Medford. "
Three bedroom with king beds, 2 & a half bathroom. 2146 square foot house.

Mountainside Chateau spectacular views and sunsets. 15 min to downtown Ashland!

10.0 out of 10, Exceptional, (5)
"Amazing stay with beautiful views. Deep in the mountains better than expected.. would recommend to anyone looking to stay in a getaway in Ashland"
Mountainside Chateau spectacular views and sunsets. 15 min to downtown Ashland!

Railroad District, steps to downtown, everything you need to enjoy Ashland!

10.0 out of 10, Exceptional, (136)
"Clean. Tidy. comfortable. Well appointed. But we left a pair of walking polls behind and would like Sugar to keep them for us and we will pick them up when we stay again in the fall of 2025. David Roberts"
Railroad District, steps to downtown, everything you need to enjoy Ashland!

Cozy creekside home with deck, 15 min to airport, shopping, 1 hr to Crater Lk.

10.0 out of 10, Exceptional, (10)
"We loved this place. It was a special time for us, visiting family (including a very ill grandparent) over christmas. This wonderful riverside home was fantastic to come back to. No complaints whatsoever. The host was great, communication was great. We are incredibly grateful. Honestly, it was likely because of what we were going through, but this house felt a bit magical to us. A sanctuary. What a blessing."
Cozy creekside home with deck, 15 min to airport, shopping, 1 hr to Crater Lk.

Beautiful & Comfortable Home in Central Point

10.0 out of 10, Exceptional, (1)
"Clean and comfortable "
The price is SAR 431
SAR 1,025 total
includes taxes & fees
24 Feb - 25 Feb
Beautiful & Comfortable Home in Central Point

Pet & family friendly 3bd house, central location, fenced yard.

10.0 out of 10, Exceptional, (1)
"Enjoyed the open floor plan. Plenty of space for the entire family and pets. Close to everything in town. We had some issues with the microwave since it kept locking us out and you have to unlug it to get it to open again. Shower was on timer and shot ice cold water with no warning. The backyard has thorny twigs which I had to pull out of my dogs paw. Those are some things that could use some improvements."
Pet & family friendly 3bd house, central location, fenced yard.

Sun Cottage Downtown Jacksonville

10.0 out of 10, Exceptional, (15)
"A little noisy with traffic, but the location was perfect. The lighting and ventilation in the kitchen was not the best, but throughout the rest of the house was great. Unfortunately, we burnt a little bit of our dinner and the smoke alarm went on (which was good) but we couldn't turn it off. Otherwise, great place and I would consider returning again."
The price is SAR 604
SAR 1,200 total
includes taxes & fees
24 Feb - 25 Feb
Sun Cottage Downtown Jacksonville

Quail Run River View Cottage!

10.0 out of 10, Exceptional, (1)
"This house was wonderful and filled all of our needs. Well stocked, very private (behind a gated driveway), and sits on a gorgeous piece of land on the river. Highly recommend! "
Quail Run River View Cottage!

New townhome next to Eagle Point Golf Course, with grill, patio, and WiFi

New townhome next to Eagle Point Golf Course, with grill, patio, and WiFi

The Phoenix House- a place to relax and rejuvenate

8.8 out of 10, Excellent, (6)
"We have stayed there twice now. Our art gallery reception was last night in Medford. Today I visited a friend in Ashland. Debbie’s Diner is very close for breakfast and Starbucks down the road. The house has an elegant feel to it, high ceilings and lots of windows to the backyard. Thank you so much."
The Phoenix House- a place to relax and rejuvenate

Cheerful 3-Bedroom home in Central Point

10.0 out of 10, Exceptional, (17)
"This house is in a very nice, quiet neighborhood but really centrally located to surrounding amenities. A beautiful and clean home - love the way it is decorated!! Jill was a great host. Her response time to any communication was almost instant."
Cheerful 3-Bedroom home in Central Point

The Rellik House and Winery

3.5 star property
9.4 out of 10, Exceptional, (3)
"Beautiful property on the winery. Nicely decorated room & large shower. Separate living, kitchenette & bedroom area. The only downside is the room we had had the parking area on one side & the winery tasting room on the other. So we kept our curtains closed. Also the hot tub was dirty. We were looking forward to using it. "
The price is SAR 550
SAR 1,271 total
includes taxes & fees
26 Mar - 27 Mar
The Rellik House and Winery

Charming home, w/hot tub, close to downtown Pet-Friendly!

10.0 out of 10, Exceptional, (34)
"super cool"
The price is SAR 1,031
SAR 2,271 total
includes taxes & fees
24 Feb - 25 Feb
Charming home, w/hot tub, close to downtown Pet-Friendly!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Ashland

A Cowslip's Belle Inn

3.0 star property
9.8 out of 10, Exceptional, (30)
"Great room. We really loved staying here."
The price is SAR 563
SAR 836 total
includes taxes & fees
24 Feb - 25 Feb
A Cowslip's Belle Inn

Charming home, w/hot tub, close to downtown Pet-Friendly!

10.0 out of 10, Exceptional, (34)
"super cool"
The price is SAR 1,031
SAR 2,271 total
includes taxes & fees
24 Feb - 25 Feb
Charming home, w/hot tub, close to downtown Pet-Friendly!

Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland

9.8 out of 10, Exceptional, (104)
"Owner very responsive to solve issues. Lovely place. Well stocked. Very comfortable. Very convenient. Thank you!"
Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.